Palladium-Catalyzed Efficient Enantioselective Synthesis of Chiral Allenes: Steric and Electronic Effects of Ligands

被引：22
作者：
Wu, Zi [1 ]
Berhal, Farouk [1 ]
Zhao, Mengmeng [2 ,3 ]
Zhang, Zhaoguo [2 ,3 ]
Ayad, Tahar [1 ]
Ratovelomanana-Vidal, Virginie [1 ]
机构：
[1] Chim ParisTech, Lab Charles Friedel, UMR CNRS 7223, F-75231 Paris 05, France
[2] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai 200240, Peoples R China
[3] State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
来源：
ACS CATALYSIS | 2014年 / 4卷 / 01期
关键词：
allene; synthetic method; asymmetric catalysis; enantioselective; palladium; ASYMMETRIC TRANSFER HYDROGENATION; KINETIC RESOLUTION; DIFLUORPHOS; DERIVATIVES; SYNPHOS; COMPLEXES; ROUTE; HYDROSILYLATION; PROSTAGLANDIN; DIPHOSPHINES;
D O I：
10.1021/cs4007827
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
Asymmetric synthesis of chiral allenes starting from prochiral substrates under mild reaction conditions promoted by Pd-SYNPHOS catalyst is reported. This protocol provides an efficient access to various enantioenriched aryl- and alkyl- substituted allenes, which are versatile building blocks of high utility to both organic and medicinal chemists, in excellent isolated yields (up to 96%) and high enatiomeric ratio values (up to 95:5). In addition, a comparative study using several C-2-symmetric atropisomeric diphosphine ligands revealed the overwhelming impact of the steric and electronic properties of the ligands for the catalytic efficiency of this process.
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页码：44 / 48
页数：5
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